JP5846136B2 - ポリイミド前駆体組成物、及びポリイミド前駆体組成物の製造方法 - Google Patents
ポリイミド前駆体組成物、及びポリイミド前駆体組成物の製造方法 Download PDFInfo
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- JP5846136B2 JP5846136B2 JP2013017934A JP2013017934A JP5846136B2 JP 5846136 B2 JP5846136 B2 JP 5846136B2 JP 2013017934 A JP2013017934 A JP 2013017934A JP 2013017934 A JP2013017934 A JP 2013017934A JP 5846136 B2 JP5846136 B2 JP 5846136B2
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- Prior art keywords
- polyimide precursor
- precursor composition
- compound
- aliphatic cyclic
- resin
- Prior art date
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- 229920001721 polyimide Polymers 0.000 title claims description 244
- 239000004642 Polyimide Substances 0.000 title claims description 235
- 239000002243 precursor Substances 0.000 title claims description 190
- 239000000203 mixture Substances 0.000 title claims description 109
- 238000004519 manufacturing process Methods 0.000 title claims description 29
- -1 tertiary amine morpholine compound Chemical class 0.000 claims description 124
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 57
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 37
- 239000003125 aqueous solvent Substances 0.000 claims description 35
- 239000011347 resin Substances 0.000 claims description 30
- 229920005989 resin Polymers 0.000 claims description 30
- 125000003277 amino group Chemical group 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 125000000962 organic group Chemical group 0.000 claims description 16
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
- 238000006358 imidation reaction Methods 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- 150000002780 morpholines Chemical class 0.000 claims description 7
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 claims description 6
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 claims description 6
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 2
- JVERADGGGBYHNP-UHFFFAOYSA-N 5-phenylbenzene-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C=2C=CC=CC=2)=C1C(O)=O JVERADGGGBYHNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 description 52
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 238000000576 coating method Methods 0.000 description 23
- 239000000523 sample Substances 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000011248 coating agent Substances 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 239000002798 polar solvent Substances 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 11
- 238000005259 measurement Methods 0.000 description 11
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 10
- 230000007423 decrease Effects 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 239000011800 void material Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 239000004020 conductor Substances 0.000 description 6
- 238000004090 dissolution Methods 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 238000000465 moulding Methods 0.000 description 6
- 239000009719 polyimide resin Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000012546 transfer Methods 0.000 description 6
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 5
- 229960002887 deanol Drugs 0.000 description 5
- 230000001965 increasing effect Effects 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 150000001491 aromatic compounds Chemical class 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000001737 promoting effect Effects 0.000 description 4
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920005575 poly(amic acid) Polymers 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000003021 water soluble solvent Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- QLVKECUOHNDWOI-UHFFFAOYSA-N 2-oxo-1,3,2$l^{5}-diazaphosphonan-2-amine Chemical compound NP1(=O)NCCCCCCN1 QLVKECUOHNDWOI-UHFFFAOYSA-N 0.000 description 2
- JEAQJTYJUMGUCD-UHFFFAOYSA-N 3,4,5-triphenylphthalic acid Chemical compound C=1C=CC=CC=1C=1C(C=2C=CC=CC=2)=C(C(O)=O)C(C(=O)O)=CC=1C1=CC=CC=C1 JEAQJTYJUMGUCD-UHFFFAOYSA-N 0.000 description 2
- ZBMISJGHVWNWTE-UHFFFAOYSA-N 3-(4-aminophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(N)=C1 ZBMISJGHVWNWTE-UHFFFAOYSA-N 0.000 description 2
- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 2
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 2
- FYYYKXFEKMGYLZ-UHFFFAOYSA-N 4-(1,3-dioxo-2-benzofuran-5-yl)-2-benzofuran-1,3-dione Chemical compound C=1C=C2C(=O)OC(=O)C2=CC=1C1=CC=CC2=C1C(=O)OC2=O FYYYKXFEKMGYLZ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000007824 aliphatic compounds Chemical class 0.000 description 2
- 150000004984 aromatic diamines Chemical class 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
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- 238000004817 gas chromatography Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 229940018564 m-phenylenediamine Drugs 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 150000004885 piperazines Chemical class 0.000 description 2
- 150000003053 piperidines Chemical class 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 150000003218 pyrazolidines Chemical class 0.000 description 2
- 150000003235 pyrrolidines Chemical class 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000007493 shaping process Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000013076 target substance Substances 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 description 1
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- CGSKOGYKWHUSLC-UHFFFAOYSA-N 1-(4-aminophenyl)-1,3,3-trimethyl-2h-inden-5-amine Chemical compound C12=CC=C(N)C=C2C(C)(C)CC1(C)C1=CC=C(N)C=C1 CGSKOGYKWHUSLC-UHFFFAOYSA-N 0.000 description 1
- YLHUPYSUKYAIBW-UHFFFAOYSA-N 1-acetylpyrrolidin-2-one Chemical compound CC(=O)N1CCCC1=O YLHUPYSUKYAIBW-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- UXOXUHMFQZEAFR-UHFFFAOYSA-N 2,2',5,5'-Tetrachlorobenzidine Chemical group C1=C(Cl)C(N)=CC(Cl)=C1C1=CC(Cl)=C(N)C=C1Cl UXOXUHMFQZEAFR-UHFFFAOYSA-N 0.000 description 1
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 1
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical group C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- OLQWMCSSZKNOLQ-UHFFFAOYSA-N 3-(2,5-dioxooxolan-3-yl)oxolane-2,5-dione Chemical compound O=C1OC(=O)CC1C1C(=O)OC(=O)C1 OLQWMCSSZKNOLQ-UHFFFAOYSA-N 0.000 description 1
- MVFJHAFRIJSPFI-UHFFFAOYSA-N 3-(3,4,5-triphenylthiophen-2-yl)benzene-1,2-diamine Chemical compound NC=1C(=C(C=CC=1)C=1SC(=C(C=1C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1)N MVFJHAFRIJSPFI-UHFFFAOYSA-N 0.000 description 1
- GDGWSSXWLLHGGV-UHFFFAOYSA-N 3-(4-aminophenyl)-1,1,3-trimethyl-2h-inden-5-amine Chemical compound C12=CC(N)=CC=C2C(C)(C)CC1(C)C1=CC=C(N)C=C1 GDGWSSXWLLHGGV-UHFFFAOYSA-N 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- RHRNYXVSZLSRRP-UHFFFAOYSA-N 3-(carboxymethyl)cyclopentane-1,2,4-tricarboxylic acid Chemical compound OC(=O)CC1C(C(O)=O)CC(C(O)=O)C1C(O)=O RHRNYXVSZLSRRP-UHFFFAOYSA-N 0.000 description 1
- IRESXNMNAGCVLK-UHFFFAOYSA-N 3-[3-(2,3-dicarboxy-4,5,6-triphenylphenyl)phenyl]-4,5,6-triphenylphthalic acid Chemical compound C=1C=CC=CC=1C=1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C(=O)O)=C(C(O)=O)C=1C(C=1)=CC=CC=1C(C(=C1C=2C=CC=CC=2)C=2C=CC=CC=2)=C(C(O)=O)C(C(O)=O)=C1C1=CC=CC=C1 IRESXNMNAGCVLK-UHFFFAOYSA-N 0.000 description 1
- TVOXGJNJYPSMNM-UHFFFAOYSA-N 3-[4-(2,3-dicarboxy-4,5,6-triphenylphenyl)phenyl]-4,5,6-triphenylphthalic acid Chemical compound C=1C=CC=CC=1C=1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C(=O)O)=C(C(O)=O)C=1C(C=C1)=CC=C1C(C(=C1C=2C=CC=CC=2)C=2C=CC=CC=2)=C(C(O)=O)C(C(O)=O)=C1C1=CC=CC=C1 TVOXGJNJYPSMNM-UHFFFAOYSA-N 0.000 description 1
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 description 1
- NRLUQVLHGAVXQB-UHFFFAOYSA-N 4-(4-amino-2-chloro-5-methoxyphenyl)-5-chloro-2-methoxyaniline Chemical group C1=C(N)C(OC)=CC(C=2C(=CC(N)=C(OC)C=2)Cl)=C1Cl NRLUQVLHGAVXQB-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G73/1032—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous characterised by the solvent(s) used
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
- C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09D179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
- C09J179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09J179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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| Application Number | Priority Date | Filing Date | Title |
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| JP2013017934A JP5846136B2 (ja) | 2013-01-31 | 2013-01-31 | ポリイミド前駆体組成物、及びポリイミド前駆体組成物の製造方法 |
| US14/038,230 US20140213724A1 (en) | 2013-01-31 | 2013-09-26 | Polyimide precursor composition and method for producing polyimide precursor composition |
| CN201310549802.3A CN103965625B (zh) | 2013-01-31 | 2013-11-07 | 聚酰亚胺前体组合物以及用于制备聚酰亚胺前体组合物的方法 |
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| JP2013017934A JP5846136B2 (ja) | 2013-01-31 | 2013-01-31 | ポリイミド前駆体組成物、及びポリイミド前駆体組成物の製造方法 |
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| JP2014148602A JP2014148602A (ja) | 2014-08-21 |
| JP2014148602A5 JP2014148602A5 (enrdf_load_stackoverflow) | 2014-10-02 |
| JP5846136B2 true JP5846136B2 (ja) | 2016-01-20 |
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| US (1) | US20140213724A1 (enrdf_load_stackoverflow) |
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| CN (1) | CN103965625B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016030760A (ja) * | 2014-07-25 | 2016-03-07 | 富士ゼロックス株式会社 | ポリイミド前駆体組成物、ポリイミド前駆体の製造方法、ポリイミド成形体、及びポリイミド成形体の製造方法 |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6007809B2 (ja) * | 2013-01-31 | 2016-10-12 | 富士ゼロックス株式会社 | ポリイミド成形体の製造方法、ポリイミド成形体、液晶配向膜、パッシベーション膜、電線被覆材、及び接着膜 |
| US9650543B2 (en) * | 2014-03-18 | 2017-05-16 | Fuji Xerox Co., Ltd. | Polyimide precursor composition, method for manufacturing polyimide molded body, and polyimide molded body |
| JP2016124956A (ja) * | 2014-12-26 | 2016-07-11 | 富士ゼロックス株式会社 | ポリアミドイミド前駆体組成物、ポリアミドイミド成形体、及びポリアミドイミド成形体の製造方法 |
| US10501579B2 (en) * | 2015-02-20 | 2019-12-10 | Sabic Global Technologies B.V. | Poly(amic acid) synthesis and conversion to high molecular weight polyimide |
| JP6701834B2 (ja) * | 2015-03-26 | 2020-05-27 | 富士ゼロックス株式会社 | 樹脂粒子分散ポリイミド前駆体溶液の製造方法、樹脂粒子分散ポリイミド前駆体溶液、樹脂粒子含有ポリイミドフィルム、多孔質ポリイミドフィルムの製造方法、及び多孔質ポリイミドフィルム |
| US9707722B2 (en) * | 2015-03-26 | 2017-07-18 | Fuji Xerox Co., Ltd. | Method for producing porous polyimide film, and porous polyimide film |
| JP6701833B2 (ja) * | 2015-03-26 | 2020-05-27 | 富士ゼロックス株式会社 | 多孔質ポリイミドフィルムの製造方法、及び多孔質ポリイミドフィルム |
| KR20180015725A (ko) * | 2015-06-03 | 2018-02-13 | 사빅 글로벌 테크놀러지스 비.브이. | 폴리이미드 전구체의 레이저-개시 적층 가공법 |
| EP3302938A1 (en) * | 2015-06-03 | 2018-04-11 | SABIC Global Technologies B.V. | Material extrusion additive manufacturing of polyimide precursor |
| JP6672667B2 (ja) | 2015-09-24 | 2020-03-25 | 富士ゼロックス株式会社 | ポリイミド前駆体組成物、ポリイミド前駆体組成物の製造方法、及びポリイミド成形体の製造方法。 |
| JP6747091B2 (ja) * | 2016-06-23 | 2020-08-26 | 富士ゼロックス株式会社 | 多孔質フィルム、及びその製造方法 |
| CN109791331B (zh) * | 2016-09-29 | 2022-05-27 | 日产化学株式会社 | 液晶取向剂、液晶取向膜和液晶表示元件 |
| JP7006033B2 (ja) | 2017-09-01 | 2022-02-10 | 富士フイルムビジネスイノベーション株式会社 | ポリイミド前駆体溶液、及びポリイミド成形体 |
| JP6900844B2 (ja) * | 2017-09-01 | 2021-07-07 | 富士フイルムビジネスイノベーション株式会社 | 無端ベルト、画像形成装置、無端ベルトユニット、及びポリイミド樹脂成形体 |
| KR102262507B1 (ko) | 2019-02-14 | 2021-06-08 | 주식회사 엘지화학 | 폴리이미드 전구체 조성물 및 이를 이용하여 제조된 폴리이미드 필름 |
| JP7245504B2 (ja) * | 2019-03-25 | 2023-03-24 | ユニチカ株式会社 | ポリイミド前駆体溶液の製造方法 |
| JP2022143803A (ja) * | 2021-03-18 | 2022-10-03 | 富士フイルムビジネスイノベーション株式会社 | ポリイミド前駆体溶液、ポリイミド前駆体溶液の製造方法、ポリイミドフィルムの製造方法、及び多孔質ポリイミドフィルムの製造方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3507765A (en) * | 1966-05-05 | 1970-04-21 | Gen Electric | Method for electrocoating a polyamide acid |
| US3663728A (en) * | 1968-07-25 | 1972-05-16 | Gen Electric | Process for producing polyamide acid and polyimides |
| CA2002147A1 (en) * | 1988-11-07 | 1990-05-07 | Shuichi Morikawa | Production process for polyimide fibers |
| US4960846A (en) * | 1990-03-09 | 1990-10-02 | Amoco Corporation | Polyimide copolymers containing 4,4'-bis(p-aminophenoxy)biphenyl and siloxane diamine moieties |
| US5202412A (en) * | 1990-10-02 | 1993-04-13 | E. I. Du Pont De Nemours And Company | Polyimide copolymer precursors |
| US5719253A (en) * | 1994-10-07 | 1998-02-17 | Unitika Ltd. | Poly(amic acid) solution and polyimide film or polymide-coated material obtained therefrom |
| WO2012008543A1 (ja) * | 2010-07-14 | 2012-01-19 | 宇部興産株式会社 | ポリイミド前駆体水溶液組成物、及びポリイミド前駆体水溶液組成物の製造方法 |
| JP5899940B2 (ja) * | 2012-01-13 | 2016-04-06 | 宇部興産株式会社 | ポリイミド前駆体水溶液組成物、及びポリイミド前駆体水溶液組成物の製造方法 |
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2013
- 2013-01-31 JP JP2013017934A patent/JP5846136B2/ja active Active
- 2013-09-26 US US14/038,230 patent/US20140213724A1/en not_active Abandoned
- 2013-11-07 CN CN201310549802.3A patent/CN103965625B/zh active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016030760A (ja) * | 2014-07-25 | 2016-03-07 | 富士ゼロックス株式会社 | ポリイミド前駆体組成物、ポリイミド前駆体の製造方法、ポリイミド成形体、及びポリイミド成形体の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20140213724A1 (en) | 2014-07-31 |
| CN103965625A (zh) | 2014-08-06 |
| JP2014148602A (ja) | 2014-08-21 |
| CN103965625B (zh) | 2018-04-03 |
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